Plant growth compositions



I Patented Apr. 26, 1949 PLANT GROWTH COMPOSITIONS David. WJJayne, Jr.,om Greenwich, Harold M. I Day, Cos Cob, and Kenneth G. Nolan, Noroton 1Heights, Conn., assignors to American Gyana mid Company, New York, N.Y., a corporation of Maine No Drawing. Application December 7, 1945,

Serial No. 633,553

'9 Claims.

The present invention relates to plant husbandry, and more particularlyto plant growthregulating compositions and methods .of regulating thegrowth characteristics of plants.

It has been discovered that the thiazyl compounds of the formula inwhich X stands fora member of the group consisting of hydrogen and ahalogen, and Y is a bivalent'hydrocarbon radical having less than ninecarbon atoms, possess remarkable and most unexpected plantgrowth-regulating properties.

In the above formula, although X may represent any one of the halogens,the preferred ones are chlorine and bromine. In regard to the nuclearhalogenated ring, it is preferred that the number of halogensubstituents be not greater than three. When themore highly halogenatedcompounds are used injury to certain types of plants may occur.

As illustrating the diversity of compounds which may be used for thepurposes of this invention, the following may be mentioned:

Benzthiazyl ether of glycollic acid 5-brombenzthiazyl ether of glycollicacid 5,6-dichlorbenzthiazyl ether of glycollic acid Benzthiazyl ether oflactic acid 5-chlorbenzthiazyl ether of hydracrylic acid Benzthiazylether of v-hydroxybutyric acid Benzthiazyl ether of a-hydroxyvalericacid 5-brombenzthiazy1 ether of a-hydroxyvaleric acid Benzthiazyl etherof a-hydroxycaproic acid Benzthiazyl ether of a-hydroxycaprylic acidfi-chlorbenzthiazyl ether of a-hydroxycaprylic acid Thiazyl compounds ofthe above type may be conveniently and economically synthesized fromavailable raw materials. For example, the benzthiazyl ether of glycollicacid is obtained by reaction ofthe sodium salt of 2-hydroxybenzothiazolewith sodium chloracetate, followed by acidification.

It is to be understood that the saltsresters, and amides of the abovecompounds which may be readily prepared by conventional methods andwhich possess substantially similar plant growthregulating properties,are included in the present invention by reasonofequivalency;

For the purpose of this invention it will also be' understood that theterm plant as used herein and in the appended claims isintended toinclude" seeds and tubers.

The compounds of this invention may be used in a variety of ways toregulate the growth characteristics of the plant. For example, they maybe applied to tubers and the like for regulating germination, tostimulate'or inhibit sprouting, or

to stimulate development of roots; they may be applied to fruit trees todelay or prevent preharvest drop; they may be applied to cuttingsandtransplanted plants or the roots thereof to stimulate root activity;they may be applied to ornamental plants to delay fall of leaves andneedles, and they may be used to chemically thin the blossoms of fruittrees or other plants.

Another method of regulating the growth characteristics of the plantconsists of incorporating the present compounds in fertilizers and plantfoods such as. for example, bone meal, peat,

phosphate, potash and urea products, or in oil,

or water insecticidal or fungicidal spraysand the like.

Different compositions may be employed in the a plication of these'plantgrowth-regulating compounds with or without carriers. For instance,

a stock solution may beprepared by dissolving the compound in an organicsolvent, This solu-- tion may then be applied in the form of an aqueousemulsion of suitable dilution. Wetting agents and/or adhesives may beincluded in these emulsions. Suitable'solvents for the compounds includediacetone alcohol, cyclohexanone, and the low molecular weightmonohydric alcohols, glycols, Cellosolves and phthalates esters. Thecompounds may also be incorporated in oils, fats, or similar vehiclessuch. as lanolin, 'paraflin oil, olive oil, hydrogenated vegetable oilsor nonvolatile petroleum oils containing not more than about 15 per centof unsaturated hydrocarbons,

- or in a finely divided inert material such'as talc,

bentonite, chalk, cotton-seed meal, fullers earth,-

The Coleus petiole technique previously described by Gardner and Cooper,The Botanical Gazette.

' vol. 105, No. 1, se t., 1943, was used for this purpose. The methodconsisted in spraying the Coleus plant (variety Trailing Queen) with afluely dispersed aqueous emulsion of the compound under test. Two daysfollowing the application of the spray, the leaf blades were removedfrom the selected petioles.- Absciss'ion records wer dated from the daythe blades were removed. The aqueous emulsion was prepared by diluting astock solution consisting of 0.5% of the compound in diacetone alcohol.-a

The tests listed in Tables 1 and 2 illustrate the surprisingly highactivity of the compounds of this invention in delaying petiole drop. Acomparison is made of the present compounds with ornaphthalene aceticacid, a known plant regulant. Aqueous emulsions of these compounds areparticularly efiective in concentrations ranging from 25 to 100 partsper million.

Table 1 4 ity while the benzthiazyl ether of glycollic acid is highlyactive. For the purpose of clarity, the formulas of the compounds listedin the table are iven as follows:

Benzthiazyl ether of glycollic acid c-o-cmcooa N Benzthiazyl ether ofthioglycollic acid 5-chlorbenzthiazyl ether of thloglycollic acid No. of

Per Cent Drop of Petioles, No. of Days Petioles Coin and pc on PlantsWater check u-naphthalene acetic acid Benghiazyl ether of glycollicacid.

Compound Per cent Drop of Petioles, v No. oi Days Water check.

ran-naphthalene acetic acid Benzthiazyl ether of glycollic acl "Lorolester of benzthiazyl ether of glycollic ac Methyl ester of benzthrazylether oi glyoollic acid Potassium salt of benztlnazyl ether 0! lycollicacid 5-brombenzthiazyl ether of glycollic a d *Lorol alcohol is aproduct of the Du Pont Company and comprises a mixture of straightchain.even-numbered carbon atom alcohols ranging from 8 to 16 carbon atomswith lauryl alcohol preponderating.

The activity of the compounds of this invention Benzoxazyl ether ofglycollic acid may be attributed to the c-o-cnicoon M N 5 linkage in themolecule. The tests given in Table 3 Benzoxazyl ether of thiogl acidverify this assumption inasmuch as the benzthiazyl ether ofthioglycollic acid, the 5-ch1orbenz- 0 thiazyl ether of thioglycollicacid, the benzoxazyl cscH,oooH ether of thioglycollic I acid and thebenzoxazyl so M ether of glycollic acid show substantially no activ-Table 3 Per cent Drop of Petioles, No. of c d i o l s Days om an m onPlants Water check 36 55.5 91.6 100 Benzthiazyl ether of glycollic acid500 38 0 0 0 0 Benzthiazyl ether of thioglgcollic acid 500 32 1005-Chlorbenzthiazyl ether 0 thioglyoolllc acid 500 36 100 Benzthiazylether of lycollic ac d 100 84 0 2. 4 27. 4 59. 5 Benzoxazyl ether of gycolllc aci 100 50. 0 85. 2 95.7 Bensoxazyl other of thioglycolllc acid100 90 65. 5 90. 0 100 The present growth-regulating compounds may beemployed effectively both inaqueous and 011- containing sprays and indust mixtures to retard the abscission of fruits such as apples, pears,peaches, grapes, etc., before harvest. With such mixtures there may beincorporated other materials serving to improve contact and coverage onthe tree or plant.

Williams early red apple trees were sprayed with aqueous emulsions of (I-naphthalene acetic acid and the benzthiazyl ether of glycollic acid.Daily drop counts were made and after the fruit was picked, the dailycumulative drop was expressed as percentage drop. Table 4 shows the percent drop cumulative at the end of the sixth day.

Table 4 Per cent Compound Drop of Apples Benzthiazyl ether olf glycollicacid 1. a-Naphthalene acetic acid l. Untreated 19.

The present compounds are also particularly adapted to the production ofparthenocarpic or seedless variety of fruit and vegetables such ascucumbers, peppers, tomatoes, eggplant, squash, etc.' This may beaccomplished by spraying the flower buds several times while floweringcontinues with a dilute aqueous suspension of the compound. Reference ishere made to applicants copending application Serial No. 633,554, filedthe said carrier bein present in maJor amount December 7, 1945,

While the invention has been described with! particular reference tospecific embodiments, it is to be understood that it is not to belimited thereto but is to be construed broadly and restricted solely bythe scope of the appended claims.

We claim:

1. A thiazyl compound having the formula in which X stands for a memberof the group consisting of hydrogen and a halogen, and Y is r a bivalenthydrocarbon radical having less than nine carbon atoms.

2. A thiazyl compound having the formula 0-0-CE1COOH M 4. The methodwhich comprises treating a plant with a thiazyl compound having theformula in which X stands for a member of the group consisting ofhydrogen and a halogen, and Y is a bivalent hydrocarbon radical havingless than nine carbon atoms.

5. The method of claim 4 wherein said thiazyl compound is a thiazylcompound having the formula in which Y is a bivalent hydrocarbon radicalhaving less than nine carbon atoms.

6. The method which comprises treating a plant with the benzthiazylether of glycollic acid.

7. A plant growth-regulating composition containing as an activeingredient a thiazyl compound having the formula in which X stands for amember of the group consisting of hydrogen and a halogen, and Y is abivalent hydrocarbon radical having less than nine carbon atoms, and aninert carrier therefor,

and the amount of said thiazyl compound present in the said compositionbeing sufficient to impart plant growth-regulating characteristicsthereto.

8. The plant growth-regulating composition of claim 7 wherein saidthiazyl compound is a thiazyl compound having the formula wherein Y is abivalent hydrocarbon radical hav- REFERENCES CITED The followingreferences are of record in file of this patent:

UNITED STATES PATENTS the Number Name Date 1,962,109 Alvord June 5, 19342,322,761 Lontz June 29, 1943 2,349,772 Ter Horst May 23, 1944 2,396,468Ladd Mar. 12, 1946 2,396,513 Jones Mar. 12, 1946

